A novel triphenylacrylonitrile based AIEgen for high contrast mechanchromism and bicolor electroluminescence

A novel thermally stable and aggregation-induced emission (AIE) active compound, 2,2'-(([1,1'-biphenyl]-4,4'-diylbis(phenylazanediyl))bis(4,1-phenylene))bis(3,3-diphenylacrylonitrile) (BP2TPAN) was synthesized through a C-N coupling reaction between 2-(4-bromophenyl)-3,3-diphenylacrylonitrile (Br-TPAN) and N,N'-diphenyl-1,4-phenylenediamine, under mild conditions using Pd(OAc)₂ and P(t-Bu)₃ as a catalyst. The BP2TPAN was characterized by nuclear magnetic resonance spectroscopy, high resolution mass spectrometry and elemental analysis. The thermal analysis showed that the glass transition and decomposition temperatures (5% weight loss) are 96 and 414 °C, respectively. The fluorescent emission peaks changes at 540 and 580 nm upon grinding were attributed to a transformation from crystal to amorphous occurring by altering the condensed state. The photoluminescence quantum yield and fluorescence lifetime of the as prepared and ground samples were 74.3 and 8.4%, 3.4 and 5.1 ns, respectively. The difference of the luminous efficiency of before and after grinding samples indicates BP2TPAN has a high contrast more importantly, both doped and nondoped OLED devices emit different color, the doped one is highly efficient and its L _max, CE_max, PE_max and EQE are up to 15 070 cd m^-2, 11.0 cd A^-1, 7.5 lm W^-1, and 3.1%, respectively.